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Two-photon induced luminescence, singlet oxygen generation, cellular uptake and photocytotoxic properties of amphiphilic Ru(II) polypyridyl-porphyrin conjugates as potential bifunctional photodynamic therapeutic agents.

Abstract
Two Ru(II) polypyridyl-porphyrin and Zn(II) porphyrin conjugates (Ru-L and Ru-Zn-L) have been synthesized and their photophysical properties studied. The two conjugates, which contained a hydrophobic tetraphenylporphyrin L conjugated via an acetylide linker at its β-position with a hydrophilic Ru(II) polypyridyl complex, showed high singlet oxygen quantum yields (>70%) and substantial two-photon absorption cross-sections (~500 GM). Ru-L gave strong emissions at ~660 and ~733 nm through linear or two-photon excitation. Solvatochromism was observed in the fluorescence spectra of Ru-L and Ru-Zn-L, where in less polar solvents (i.e., toluene and dichloromethane) their fluorescence emissions became slightly blue-shifted with a 3-fold reduction in intensity relative to those observed in polar solvents (i.e., acetonitrile and methanol). Cell-based studies of these complex conjugates were conducted using human nasopharyngeal carcinoma HK-1 and cervical carcinoma HeLa cells on which Ru-L showed rapid cellular uptake, low dark-cytotoxicity, and high photo-cytotoxicity. Furthermore, Ru-L can be excited and emits in the "biological window"in vitro, making it a potential potent new generation photodynamic therapeutic agent capable of singlet oxygen generation and in vitro near-infrared emission.
AuthorsJingXiang Zhang, Ka-Leung Wong, Wai-Kwok Wong, Nai-Ki Mak, Daniel W J Kwong, Hoi-Lam Tam
JournalOrganic & biomolecular chemistry (Org Biomol Chem) Vol. 9 Issue 17 Pg. 6004-10 (Sep 07 2011) ISSN: 1477-0539 [Electronic] England
PMID21748193 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antineoplastic Agents
  • Cytotoxins
  • Metalloporphyrins
  • Photosensitizing Agents
  • Ru(II) polypyridyl-porphyrin
  • Ru-Zn-polypyridyl-porphyrin
  • Singlet Oxygen
Topics
  • Antineoplastic Agents (chemistry, pharmacokinetics, pharmacology)
  • Cell Line, Tumor
  • Cytotoxins (chemistry, pharmacokinetics, pharmacology)
  • Humans
  • Luminescence
  • Metalloporphyrins (chemistry, pharmacokinetics, pharmacology)
  • Neoplasms (drug therapy)
  • Photochemotherapy
  • Photosensitizing Agents (chemistry, pharmacokinetics, pharmacology)
  • Singlet Oxygen (metabolism)

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